X0407 4 2023-04-04 0 0001564406 Oak Street Health, Inc. OSH 0001793313 PRICE GEOFFREY M C/O OAK STREET HEALTH, INC. 30 W. MONROE ST., SUITE 1200 CHICAGO IL 60603 1 1 0 0 Chief Innovation Officer 0 Common Stock, $0.001 par value 2023-04-04 4 M 0 50000 21.00 A 3934042 D Common Stock, $0.001 par value 2023-04-04 4 S 0 50000 38.8031 D 3884042 D Common Stock, $0.001 par value 1080970 I By Price-Uhl Living Trust Employee Stock Option (Right to Buy) 21.00 2023-04-04 4 M 0 50000 0.00 D 2020-08-05 Common Stock, par value $0.001 50000 1932609 D The option exercises and sales reported in this Form 4 were effected pursuant to a Rule 10b5-1 trading plan previously adopted by the Reporting Person. The price reported in column 4 is a weighted average price. The shares were sold in multiple transactions at prices ranging from $38.795 to $38.830, inclusive. The Reporting Person undertakes to provide to Oak Street Health, Inc., any security holder of Oak Street Health, Inc., or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares sold at each price within the ranges set forth in this footnote (2). The reported securities include the aggregate options, all of which were issued at the time of the Issuer's initial public offering, held by the Reporting Person, a portion of which remains subject to vesting. /s/ Robert Guenthner, attorney-in-fact for Geoffrey Price 2023-04-06